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Pursuing a relationship with my boss

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I am a dispatcher. My boss, although not directly, is the sheriff. I have "liked" her for months, long before I got this job. She told me she had feelings for me through text last week. There is no direct policy against fraternization but she does have a "not serious" boyfriend. And she is still my boss no matter how indirectly. We text a lot and the discussion often becomes pretty sexual. My issue is, I really do like her. I would really like to see where this goes without getting her or myself in to any sketchy situations. In my opinion, I feel like I can keep professional and personal matters separate especially as we work opposite shifts and rarely see each other. My main concern is the boyfriend. I don't know him or the level of seriousness in their relationship. She is coming over to drink on Friday night and I am concerned about my ability to remain neutral. I've heard all the "don't date your boss" advice and I guess I just want to know if anyone has been in a situation like this that didn't end up in flames?

Pursuing a relationship with my boss

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i hear you out mate
these dating the boss thing is sketchy but sometimes you have to go for it . and it is better that you work at different times as this will keep a professional work enviroment easy to work in without distractions. and if she really like you then she will dump this guy . this girl i liked her for ages my next door neighbour in fact , she never said she did but we started chatting on phone and some of my friend were bugging me to ask her out and her friends told me to as well. but on problem she already had a boyfriend. i asked her out and the next day she dumped her boyfriend and all was happy. what im trying to say is that don't stay neutral go for it if you like her you have to do these things. if you have any worrys just ask i will try to help but yeah hopefully this will help and let me know what happens .

Pursuing a relationship with my boss

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1. As you admit, you haven't a clue whether her boyfriend is or isn't serious. She's obviously not going to tell you if he is, is she (think about it). So let's assume the fact of his existence in that role (enough to be called 'boyfriend' rather than 'friend') is proof enough that, oh, yes, he damn well is.

Are you comfortable with becoming a cheap mistress figure, as well as doing the dirty on one of your brethren?

2. Equally, are you comfortable with the idea that her boyfriend might, for all you know, be 6'5", built like a brick sh*thouse, and short on tolerance and self-control?... possibly with a posse of very loyal, likeminded and like-built mates?

3. Beware no direct policy on this score. It allows too much scope for stretching the tacit beyond all recognition.

4. I have seen many men, not just women, demoted, passed up for promotion, fired or manoeuvred out of a job using some or other plausible excuse by disgruntled, sated, later-embarrassed or newly distracted female bosses... the same boss who is going to be approached by your next employer for a (wait for it) REFERENCE.

5. How did she get to become the boss, do you suppose? Hard-nosed? Mercenary? Clever at influencing, manipulating and out-foxing people?

You are starting out already on the backfoot - which is where you'll forever remain...even if you and she ended up a couple (dynamic stuck set in concrete). Great. "Relationship Underdog, anyone?"

6. For god's sake empty your bags before you go! If you really have to go, that is. Trouble is, you DO, don't you. Think about how displeased (and possibly out for revenge) (you've only seen her in-situ and positive side) she's going to feel if you reject her by cancelling. Time to act like an inept a*sehole with antisocial habits, methinks.

7. Are you really that impeded when it comes to seeking other fish, ones who CAN'T detriment your current job and future career (not to mention your forevermore conscience)? Or are you acting-out in terms of the slow route to getting yourself fired rather than resigning?

8. I only know ONE such dalliance (out of about 25 or so) that ended in a relationship. Refer to 'relationship underdog, anyone?'. Lose/Lose.

9. If you don't treasure that job, the solution is to chuck it in and get another (and ask her to hold) so that you enter the relationship ground AN EQUAL and an upstanding. HOWEVER, if she can cheat on him, then.... (Yup.)

Have I got you thinking yet?

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